Efficient Negishi Coupling Reactions of Aryl Chlorides Catalyzed by Binuclear and Mononuclear Nickel−N-Heterocyclic Carbene Complexes
Authors:
- 8 October 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 73 (21) , 8497-8501
Abstract
We describe the first nickel-N-heterocyclic carbene catalyzed Negishi cross-coupling reaction of a variety of unactivated aryl chlorides, heterocyclic chlorides, aryl dichlorides, and vinyl chloride. The mononuclear and binuclear nickel-NHC complexes supported by heteroarene-functionalized NHC ligands are found to be highly efficient for the coupling of unactivated aryl chlorides and organozinc reagents, leading to biaryls and terphenyls in good to excellent yields under mild conditions. For all aryl chlorides, the binuclear nickel catalysts show activities higher than those of mononuclear nickel complexes because of possible bimetallic cooperative effect.Keywords
This publication has 67 references indexed in Scilit:
- Negishi Cross-Couplings of Unsaturated Halides Bearing Relatively Acidic Hydrogen Atoms with Organozinc ReagentsOrganic Letters, 2008
- Palladium(II) and Gold(I) Complexes of a New O-Functionalized N-Heterocyclic Carbene Ligand: Synthesis, Structures, and Catalytic ApplicationOrganometallics, 2007
- Palladium−Tetraphosphine as Catalyst Precursor for High-Turnover-Number Negishi Cross-Coupling of Alkyl- or Phenylzinc Derivatives with Aryl BromidesOrganometallics, 2006
- Synthesis, Structural Characterization, Computational Study, and Catalytic Activity of Metal Complexes Based on Tetradentate Pyridine/N-Heterocyclic Carbene LigandOrganometallics, 2005
- Room-Temperature Negishi Cross-Coupling of Unactivated Alkyl Bromides with Alkyl Organozinc Reagents Utilizing a Pd/N-Heterocyclic Carbene CatalystThe Journal of Organic Chemistry, 2005
- Palladium-Catalyzed Cross-Coupling Reactions with Zinc, Boron, and Indium Exhibiting High Turnover Numbers (TONs): Use of Bidentate Phosphines and Other Critical Factors in Achieving High TONs†Organometallics, 2005
- Reversibly Addressing an Allosteric Catalyst In Situ: Catalytic Molecular TweezersAngewandte Chemie International Edition, 2004
- Highly Stereoselective Synthesis of (1E)‐2‐Methyl‐1,3‐dienes by Palladium‐Catalyzed trans‐Selective Cross‐Coupling of 1,1‐Dibromo‐1‐alkenes with Alkenylzinc ReagentsAngewandte Chemie International Edition, 2004
- New Practical Syntheses of 4‘-Methylbiphenyl-2-carbonitrile and -2-carbaldehydeThe Journal of Organic Chemistry, 1999
- The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]Angewandte Chemie International Edition, 1986